EP1853571A1 - Formes cristallines d un intermédiaire du linézolide - Google Patents

Formes cristallines d un intermédiaire du linézolide

Info

Publication number
EP1853571A1
EP1853571A1 EP06735977A EP06735977A EP1853571A1 EP 1853571 A1 EP1853571 A1 EP 1853571A1 EP 06735977 A EP06735977 A EP 06735977A EP 06735977 A EP06735977 A EP 06735977A EP 1853571 A1 EP1853571 A1 EP 1853571A1
Authority
EP
European Patent Office
Prior art keywords
oxo
oxazolidinyl
fluorophenyl
morpholinyl
crystalline
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06735977A
Other languages
German (de)
English (en)
Inventor
Tamas Koltai
Tamar Nidam
Viviana Braude
Serguei Fine
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Teva Pharmaceutical Industries Ltd
Original Assignee
Teva Pharmaceutical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Teva Pharmaceutical Industries Ltd filed Critical Teva Pharmaceutical Industries Ltd
Publication of EP1853571A1 publication Critical patent/EP1853571A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to the solid state chemistry of the linezolid intermediate S-N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine.
  • Linezolid [(S)-N-[[3-(3-Fluoro-4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl] acetamide] is an antimicrobial agent.
  • Linezolid is an oxazolidinone, having the empirical formula C 16 H 2 QFN 3 O 4 and the following structure (I):
  • Crystalline Form II linezolid is disclosed in U.S. Patent No. 6,559,305.
  • Linezolid is marketed in the United States by Pfizer, Inc. as an injection, tablets, and oral suspension under the name ZYVOX®. Its main indications are nosocomial pneumonia, skin and skin-structure infections, and vancomycin-resistant Enterococcus faecium infections.
  • the present invention relates to the solid state physical properties of an intermediate of linezolid, S-N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II). These properties can be influenced by controlling the conditions under which S- N-(4-morpholinyl-3-fl.uorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) is obtained in solid form.
  • One important solid state property is its rate of dissolution in aqueous fluid or its behavior on compaction and its storage stability.
  • the polymorphic form may give rise to thermal behavior different from that of the amorphous material or another polymorphic form. Thermal behavior is measured in the laboratory by such techniques as capillary melting point, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) and can be used to distinguish some polymorphic forms from others.
  • TGA thermogravimetric analysis
  • DSC differential scanning calorimetry
  • a particular polymorphic form may also give rise to distinct spectroscopic properties that may be detectable by powder X-ray crystallography, solid state 13 C NMR spectrometry and infrared spectrometry. Summary of the Invention
  • the present invention is based on the finding that the linezolid intermediate S-N-(4- morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) can be obtained in at least three different crystalline forms: Form A, Form B, and Form C.
  • the present invention provides a crystalline S-N-(4-morpholinyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) referred to herein as Form A, characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 13.2 ⁇ 0.2, 14.8 ⁇ 0.2, 15.1 ⁇ 0.2, and 25.0 ⁇ 0.2 degrees 2 theta or substantially as indicated in Figure 1.
  • PXRD powder X-ray diffraction
  • the present invention provides a crystalline S-N-(4-morpholinyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) referred to herein as Form B, characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 15.6 ⁇ 0.2, 19.2 ⁇ 0.2, 22.5 ⁇ 0.2, and 24.3 ⁇ 0.2 degrees 2 theta or substantially as indicated in Figure 2.
  • PXRD powder X-ray diffraction
  • the present invention provides a crystalline S-N-(4-morpholinyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) referred to herein as Form C, characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 5.8 ⁇ 0.2, 11.5 ⁇ 0.2, 19.6 ⁇ 0.2, and 26.3 ⁇ 0.2 degrees 2 theta or substantially as indicated in Figure 3.
  • PXRD powder X-ray diffraction
  • Figure 1 shows the powder X-ray diffractogram of linezolid intermediate amine (II) Form A.
  • Figure 2 shows the powder X-ray diffractogram of linezolid intermediate amine (II) Form B.
  • Figure 3 shows the powder X-ray diffractogram of linezolid intermediate amine (II) Form C.
  • the present invention is based on the finding that the linezolid intermediate S-N-(4- morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) can be obtained in at least three different crystalline forms: Form A, Form B, and Form C.
  • the present invention provides novel solid crystalline forms of S-N-(4-morpholinyl-3- fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II), referred to herein as Form A, Form B, and Form C.
  • the crystalline Forms A, B, and C may be distinguished by their respective powder X-ray diffraction (PXRD) patterns.
  • the crystalline forms have characteristic PXRD peak positions in the range of 2-40 degrees two theta. Crystalline Forms A, B, and C can be identified by these characteristic peak positions and the identity and quantify of their crystalline impurities can also be determined.
  • the present invention provides a crystalline S-N-(4-morpholinyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-niethyl amine (II) referred to herein as Form A, characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 13.2 ⁇ 0.2, 14.8 ⁇ 0.2, 15.1 ⁇ 0.2, and 25.0 ⁇ 0.2 degrees 2 theta.
  • Form A may be further characterized by PXRD peaks at 3.0 ⁇ 0.2, 16.1 ⁇ 0.2, 17.9 ⁇ 0.2. 19.3 ⁇ 0.2, and 23.0 ⁇ 0.2 degrees 2 theta, substantially as depicted in Figure 1.
  • the present invention provides a crystalline S-N-(4-morpholinyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) referred to herein as Form B, characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 15.6 ⁇ 0.2, 19.2 ⁇ 0.2, 22.5 ⁇ 0.2, and 24.3 ⁇ 0.2 degrees 2 theta.
  • Form B may be further characterized by PXRD peaks at 7.2 ⁇ 0.2, 14.6 ⁇ 0.2, 16.5 ⁇ 0.2, 20.1 ⁇ 0.2, and 23.0 ⁇ 0.2 degrees 2 theta, substantially as depicted in Figure 2.
  • the present invention provides a crystalline S-N-(4-morpholinyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) referred to herein as Form C, characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 5.8 ⁇ 0.2, 11.5 ⁇ 0.2, 19.6 ⁇ 0.2, and 26.3 ⁇ 0.2 degrees 2 theta.
  • Form C may be further characterized by PXRD peaks at 13.2 ⁇ 0.2, 20.4 ⁇ 0.2, 21.6 ⁇ 0.2, 22.3 ⁇ 0.2, 23.0 ⁇ 0.2, and 23.8 ⁇ 0.2 degrees 2 theta, substantially as depicted in Figure 3.
  • the crystalline Forms A, B, and C of S-N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5- oxazolidinyl-methyl amine (II) of the present invention maybe substantially pure with respect to other crystalline forms, i.e., the novel forms contain less than about 10%, preferably less than about 5%, and even more preferably less than about 1% (by weight) of other crystalline forms of S-N-(4-morpholmyl-3-fluorophenyl)-2-oxo-5- oxazolidinyl-methyl amine (II).
  • the novel crystalline forms contain less than about 10%, preferably less than about 5%, and even more preferably less than about 1% (by weight) of amorphous S-N-(4-morpholinyl-3-fiuorophenyl)-2- oxo-5-oxazolidinyl-methyl amine (II).
  • the present invention is not intended to encompass true solutions of S-N-(4- morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) wherein the crystal structure of the novel crystalline Forms A, B, and C and the properties that distinguish the novel crystalline forms of the present invention are lost.
  • the preferred form of the present invention is that of solid forms of crystalline Forms A, B, and C.
  • the use of the novel forms to prepare solutions is considered to be within the contemplation of the invention.
  • Powder X-ray diffraction data were obtained by methods known in the art using a SCINTAG® powder X-ray diffractometer model XTRA® equipped with a solid state detector. Copper radiation of 1.5418 A was used. A round aluminum sample holder with round zero background quartz plate was used, with cavity of 25(diameter)* 0.5 (depth) mm. The obtained characteristic peaks were in the range of 2-40 degrees two theta.
  • Example 1 Preparation of intermediate amine (H) crystalline Form B hi a IL reactor, 6 g R-N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl ⁇ methyl azide (III) was charged with 150 ml ethyl acetate, followed by 0.6 g 10% Pd/C. The system was flushed 3 times with nitrogen and 3 times with hydrogen. The pressure of hydrogen was set to 1.5 atm. The reaction mixture was stirred at RT and the reaction followed by TLC or HPLC until completion.
  • Example 3 preparation of intermediate amine (II) crystalline Form A hi a three necked flask, 6.4 g R-N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5- oxazolidinyl-methyl azide (III) was charged, followed by 2.5 g ammonium formate, 23 ml ethanoL and 2.6 g zinc powder. The reaction mixture was stirred at RT and the reaction followed by TLC or HPLC until completion. 60 ml acetone were then added.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Virology (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Sampling And Sample Adjustment (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne de nouvelles formes cristallines de l’intermédiaire du linézolide S-N-(4-morpholinyl-3-fluorophényl)-2-oxo-5-oxazolidinyl-méthylamine auquel on réfère ici comme la forme A, la forme B et la forme C.
EP06735977A 2005-02-24 2006-02-24 Formes cristallines d un intermédiaire du linézolide Withdrawn EP1853571A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US65664605P 2005-02-24 2005-02-24
US65677805P 2005-02-24 2005-02-24
US69082205P 2005-06-14 2005-06-14
PCT/US2006/006529 WO2006091777A1 (fr) 2005-02-24 2006-02-24 Formes cristallines d’un intermédiaire du linézolide

Publications (1)

Publication Number Publication Date
EP1853571A1 true EP1853571A1 (fr) 2007-11-14

Family

ID=36498839

Family Applications (3)

Application Number Title Priority Date Filing Date
EP06735895A Withdrawn EP1866295A2 (fr) 2005-02-24 2006-02-23 Procedes de preparation d'intermediaire linezolid
EP06735977A Withdrawn EP1853571A1 (fr) 2005-02-24 2006-02-24 Formes cristallines d un intermédiaire du linézolide
EP06721050A Withdrawn EP1861383A2 (fr) 2005-02-24 2006-02-24 Bis-linezolide isole, sa preparation et son utilisation comme norme de reference

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP06735895A Withdrawn EP1866295A2 (fr) 2005-02-24 2006-02-23 Procedes de preparation d'intermediaire linezolid

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP06721050A Withdrawn EP1861383A2 (fr) 2005-02-24 2006-02-24 Bis-linezolide isole, sa preparation et son utilisation comme norme de reference

Country Status (8)

Country Link
US (4) US7291614B2 (fr)
EP (3) EP1866295A2 (fr)
JP (2) JP2008530028A (fr)
CA (2) CA2602073A1 (fr)
IL (3) IL183379A0 (fr)
MX (3) MX2007010141A (fr)
TW (1) TW200640886A (fr)
WO (3) WO2006091731A2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011114210A2 (fr) 2010-03-15 2011-09-22 Jubilant Life Sciences Limited Procédés de préparation de linézolide
WO2011137222A1 (fr) 2010-04-30 2011-11-03 Indiana University Research And Technology Corporation Procédés de préparation de linézolide
EP2690100A1 (fr) 2010-08-11 2014-01-29 Synhton B.V. Proécdé pour la préparation de Linezolid
WO2012019632A1 (fr) 2010-08-11 2012-02-16 Synthon B.V. Procédé pour fabriquer du linézolid
US9567307B2 (en) 2011-01-07 2017-02-14 The Regents Of The University Of California Amination of aryl alcohol derivatives
WO2013111048A1 (fr) 2012-01-24 2013-08-01 Jubilant Life Sciences Limited Procédé amélioré de préparation de la forme cristalline stable i du linézolide, pratiquement exempte de solvant résiduel
ES2603252T3 (es) 2012-11-09 2017-02-24 Synthon Bv Proceso para preparar linezolid
EP2989097A4 (fr) * 2013-04-25 2017-11-08 Symed Labs Limited Procédés améliorés pour la préparation de linézolide par utilisation de nouveaux intermédiaires
AR099354A1 (es) 2013-11-15 2016-07-20 Akebia Therapeutics Inc Formas sólidas de ácido {[5-(3-clorofenil)-3-hidroxipiridin-2-carbonil]amino}acético, composiciones, y sus usos
CN109265407B (zh) * 2018-10-23 2020-05-29 扬子江药业集团北京海燕药业有限公司 一种双利奈唑胺的合成方法
CN109444294B (zh) * 2018-12-27 2021-06-22 苏州莱奥生物技术有限公司 一种分离利奈唑胺和其手性异构体的高效液相色谱方法

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Also Published As

Publication number Publication date
US20060252932A1 (en) 2006-11-09
IL183379A0 (en) 2007-09-20
IL184038A0 (en) 2007-10-31
US20060258655A1 (en) 2006-11-16
MX2007010141A (es) 2007-09-27
WO2006091848A3 (fr) 2006-12-28
IL183380A0 (en) 2007-09-20
US20070021417A1 (en) 2007-01-25
CA2602073A1 (fr) 2006-08-31
WO2006091731A3 (fr) 2006-10-19
TW200640886A (en) 2006-12-01
MX2007010136A (es) 2007-09-27
US20080045707A1 (en) 2008-02-21
EP1861383A2 (fr) 2007-12-05
WO2006091731A2 (fr) 2006-08-31
CA2588876A1 (fr) 2006-08-31
WO2006091848A2 (fr) 2006-08-31
MX2007010143A (es) 2007-09-27
JP2008530028A (ja) 2008-08-07
WO2006091777A1 (fr) 2006-08-31
EP1866295A2 (fr) 2007-12-19
US7291614B2 (en) 2007-11-06
JP2008530144A (ja) 2008-08-07
WO2006091848A9 (fr) 2006-11-09

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